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It is a piece by piece nature. I am still doing it, even though I consider myself fortunate with the gear I have.
You forget to mention loans/investors. It can be dangerous, but if you meet the right people or bank with the "nice/forgiving" administrators, you can actually make that leap from mid-end to high end fairly rapidly. The dangerous part about it is living up to the quality and expectation that comes with that move. It'll be either a break even or a quick bomb that'll blow up in your face within the first year.
Playing it safe, you can save, and save, and save. But that takes a long time. If you're young and depending on your income, it could end up being a nice retirement gift for yourself...
One alternative, is to actually find a facility that "rents" itself and its gear. Mark that price, and add yours when talking to your clients. You get the benefit of a good room, good gear, and better techniques from working in that environment. If you can wrangle in clients regularly, I'm sure the studio owner might decide on a house engineer (another way of breaking into the high end with little committment). If not, you'll be certain that you can tackle a high end studio construction easily with your developed skills.
With all this info, you're probably wondering where the hell I came from. I'm actually ending my 3rd and beginning my 4th month as a "studio" engineer with an "investor". I can't say for sure that it is high end with certainty, due to various ideas of what constitutes that. It is exciting, but things seems to be moving at baby steps. Kinda scary when thinking about it, but working tends to solidify my convictions that I'm doing the right thing.
Hope this helps get some ideas out for you and others to maybe make some big plans for the future.
-John
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